On the surface this looks like a good opportunity.

Had the tenant have a bit more skin in the game for fixing them.

That right there, made my shirt tight and my skin green thinking about the time wasted.  

@Rashad ReedI would start planning your exit strategy and work backwards from there, as long as you have skin in the game the hard money will be the easy part you just need to have a great deal, which can be a great thing too because if its not a great deal the hard money lender wont allow you to more forward with it, if you are planning to hold I would advise you to be prequalified with exit lender as hard money is usually short term 6-12 months.

A deal that may look good on the surface might actually have many flaws.

I think most will want you to have some skin in the game.

I also make sure the borrower has some skin in the game. 

Baltimore has a program called "Vacants to Value" which on the surface does not specify any SFR versus MFR...

The borrower's desire to qualify, and get repair money, seem to be enough "skin in the game" to follow this to the end.The other option was to dump the property at a loss.

About two years ago, I had a rubber membrane surface installed over the original roof and have had no leaks since then.